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TAK-700 (R-form)

(CAS: 752243-39-3)

Suppliers of TAK-700 (R-form)

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Shanghai Haoyuan Chemexpress Co., Ltd. [email protected] +86 (21) 5187-0955 / +86 (21) 5895-5995 China

Fax: +86 (21) 5895-5996Purity: Brand:

Price and Availability: USD135/5mg () USD225/10mg ()

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Background Information of TAK-700 (R-form)

Orteronel (TAK-700 R-form) is a naphthylmethylimidazole derivative.Orteronel (TAK-700 R-form) is a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer. IC50 value: Target: 17,20-lyase

Solubility of TAK-700 (R-form)

Solubility Sources

Storage Condition of TAK-700 (R-form)

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MSDS Information

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Quality Control and Spectral Data

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
TAK-700 (R-form) Millennium Pharmaceuticals Inc; PPD Development (S) Pte Ltd; Takeda Bio Development Center Ltd Hormone refractory prostate cancer 2010/11/30 2013/7/31 Phase 3 Clinical
TAK-700 (R-form) Millennium Pharmaceuticals Inc Hormone refractory prostate cancer 2010/10/31 2013/6/30 Phase 3 Clinical
TAK-700 (R-form) SWOG Metastatic prostate cancer 2013/3/31 2020/7/01 Phase 3 Clinical
TAK-700 (R-form) Radiation Therapy Oncology Group Hormone dependent prostate cancer 2012/5/31 2014/10/01 Phase 3 Clinical
TAK-700 (R-form) Schweizerische Arbeitsgruppe fuer angewandte Krebsforschung; Swiss Group for Clinical Cancer Research Hormone refractory prostate cancer 2012/9/30 2020/12/31 Phase 3 Clinical
TAK-700 (R-form) - No Development Reported

Chemical Information

M.Wt Formula CAS No. Synonyms
307.35 C18H17N3O2 752243-39-3 Orteronel;TAK700;TAK 700; (R)-6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide

Structure Information of TAK-700 (R-form)

Smiles O=C(NC)C1=CC=C2C=C([[email protected]]3(O)CCN4C=NC=C43)C=CC2=C1
InChI InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m1/s1

Related Products

Other Form Products of TAK-700 (R-form)

Name CAS Formula Suppliers
Orteronel (racemate) 426219-18-3 C18H17N3O2 4
TAK-700 (salt) 426219-53-6 C28H28N4O7 2

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Orteronel (racemate) 426219-18-3 C18H17N3O2 4
TAK-700 (salt) 426219-53-6 C28H28N4O7 2
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Chemical and Physical Properties

Appearance: Melting point:
Boiling point: Flash Point:
Water Solubility: Solubility:
Density:1.35 Merck:
BRN: Refractive Index:
Vapour: EINECS:
Optical Rotation: alpha:

Reference

[1].Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer By Kaku, Tomohiro; Hitaka, Takenori; Ojida, Akio; Matsunaga, Nobuyuki; Adachi, Mari; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Okuda, Teruaki; et al From Bioorganic & Medicinal Chemistry (2011), 19(21), 6383-6399.
A novel naphthylmethylimidazole derivative 1 and its related compounds were identified as 17,20-lyase inhibitors. Based on the structure-activity relationship around the naphthalene scaffold and the results of a docking study of 1a in the homology model of 17,20-lyase, the 6,7-dihydro-5H-pyrrolo[1,2-c]imidazole derivative (+)-3c was synthesized and identified as a potent and highly selective 17,20-lyase inhibitor. Biological evaluation of (+)-3c at a dose of 1mg/kg in a male monkey model revealed marked reductions in both serum testosterone and dehydroepiandrosterone concentrations. Therefore, (+)-3c (termed orteronel [TAK-700]) was selected as a candidate for clinical evaluation and is currently in phase III clinical trials for the treatment of castration-resistant prostate cancer....

[2].Gurav S, Police A, Zainuddin M, Punde RR, Dewang P, V C, Kethiri RR, Rajagopal S, Mullangi R. Development and validation of an enantioselective LC-MS/MS method to quantify enantiomers of (±)-TAK-700 in rat plasma: lack of in vivo inversion of (+)-TAK-700 (Orteronel) to its antipode. Biomed Chromatogr. 2012 Jun 19. doi: 10.1002/bmc.2764.
A highly sensitive, specific and enantioselective assay has been developed and validated for the estimation of TAK-700 enantiomers [(+)-TAK-700 and (-)-TAK-700] in rat plasma on LC-MS/MS-ESI in the positive-ion mode. Liquid-liquid extraction was used to extract (±)-TAK-700 enantiomers and IS (phenacetin) from rat plasma. TAK-700 enantiomers were separated using methanol and 5?mm ammonium acetate (80:20, v/v) at a flow rate of 0.7?mL/min on a Chiralcel OJ-RH column. The total run time was 7.0?min and the elution of (+)-TAK-700, (-)-TAK-700 and IS occurred at 3.71, 4.45 and 4.33?min, respectively. The MS/MS ion transitions monitored were m/z 308.2?→?95.0 for TAK-700 and m/z 180.2?→?110.1 for IS. The standard curves for TAK-700 enantiomers were linear (r(2) ?>?0.998) in the concentration range 2.01-2015?ng/mL for each enantiomer. The inter- and intra-day precisions were in the ranges 3.74-7.61 and 2.06-8.71% and 3.59-9.00 and 2.32-11.0% for (+)-TAK-700 and (-)-TAK-700, respectively. Both the enantiomers were found to be stable in a battery of stability studies. This novel method was applied to the study of stereoselective oral pharmacokinetics of (+)-TAK-700 and it was unequivocally demonstrated that (+)-TAK-700 does not undergo chiral inversion to its antipode in vivo.

[3].Yamaoka M, Hara T, Hitaka T, Kaku T, Takeuchi T, Takahashi J, Asahi S, Miki H, Tasaka A, Kusaka M. Orteronel (TAK-700), a novel non-steroidal 17,20-lyase inhibitor: effects on steroid synthesis in human and monkey adrenal cells and serum steroid levels in cynomolgus monkeys. J Steroid Biochem Mol Biol. 2012 Apr;129(3-5):115-28.
Surgical or pharmacologic methods to control gonadal androgen biosynthesis are effective approaches in the treatment of a variety of non-neoplastic and neoplastic diseases. For example, androgen ablation and its consequent reduction in circulating levels of testosterone is an effective therapy for advanced prostate cancers. Unfortunately, the therapeutic effectiveness of this approach is often temporary because of disease progression to the 'castration resistant' (CRPC) state, a situation for which there are limited treatment options. One mechanism thought to be responsible for the development of CRPC is extra-gonadal androgen synthesis and the resulting impact of these residual extra-gonadal androgens on prostate tumor cell proliferation. An important enzyme responsible for the synthesis of extra-gonadal androgens is CYP17A1 which possesses both 17,20-lyase and 17-hydroxylase catalytic activities with the 17,20-lyase activity being key in the androgen biosynthetic process. Orteronel (TAK-700), a novel, selective, and potent inhibitor of 17,20-lyase is under development as a drug to inhibit androgen synthesis. In this study, we quantified the inhibitory activity and specificity of orteronel for testicular and adrenal androgen production by evaluating its effects on CYP17A1 enzymatic activity, steroid production in monkey adrenal cells and human adrenal tumor cells, and serum levels of dehydroepiandrosterone (DHEA), cortisol, and testosterone after oral dosing in castrated and intact male cynomolgus monkeys. We report that orteronel potently suppresses androgen production in monkey adrenal cells but only weakly suppresses corticosterone and aldosterone production; the IC(50) value of orteronel for cortisol was ~3-fold higher than that for DHEA. After single oral dosing, serum levels of DHEA, cortisol, and testosterone were rapidly suppressed in intact cynomolgus monkeys. In castrated monkeys treated twice daily with orteronel, suppression of DHEA and testosterone persisted throughout the treatment period. In both in vivo models and in agreement with our in vitro data, suppression of serum cortisol levels following oral dosing was less than that seen for DHEA. In terms of human CYP17A1 and human adrenal tumor cells, orteronel inhibited 17,20-lyase activity 5.4 times more potently than 17-hydroxylase activity in cell-free enzyme assays and DHEA production 27 times more potently than cortisol production in human adrenal tumor cells, suggesting greater specificity of inhibition between 17,20-lyase and 17-hydroxylase activities in humans vs monkeys. In summary, orteronel potently inhibited the 17,20-lyase activity of monkey and human CYP17A1 and reduced serum androgen levels in vivo in monkeys. These findings suggest that orteronel may be an effective therapeutic option for diseases where androgen suppression is critical, such as androgen sensitive and CRPC.

[4].Kaku T, Hitaka T, Ojida A, Matsunaga N, Adachi M, Tanaka T, Hara T, Yamaoka M, Kusaka M, Okuda T, Asahi S, Furuya S, Tasaka A. Discovery of orteronel (TAK-700), a naphthylmethylimidazole derivative, as a highly selective 17,20-lyase inhibitor with potential utility in the treatment of prostate cancer. Bioorg Med Chem. 2011 Nov 1;19(21):6383-99.
A novel naphthylmethylimidazole derivative 1 and its related compounds were identified as 17,20-lyase inhibitors. Based on the structure-activity relationship around the naphthalene scaffold and the results of a docking study of 1a in the homology model of 17,20-lyase, the 6,7-dihydro-5H-pyrrolo[1,2-c]imidazole derivative (+)-3c was synthesized and identified as a potent and highly selective 17,20-lyase inhibitor. Biological evaluation of (+)-3c at a dose of 1mg/kg in a male monkey model revealed marked reductions in both serum testosterone and dehydroepiandrosterone concentrations. Therefore, (+)-3c (termed orteronel [TAK-700]) was selected as a candidate for clinical evaluation and is currently in phase III clinical trials for the treatment of castration-resistant prostate cancer.

[5].Adamo V, Noto L, Franchina T, Chiofalo G, Picciotto M, Toscano G, Caristi N. Emerging targeted therapies for castration-resistant prostate cancer. Front Endocrinol (Lausanne). 2012;3:73.
Until recently, few therapeutic options were available for patients with castration-resistant prostate cancer (CRPC). Since 2010, four new molecules with a demonstrated benefit (sipuleucel-T, cabazitaxel, abiraterone, and denosumab) have been approved in this setting, and to-date several other agents are under investigation in clinical trials. The purpose of this review is to present an update of targeted therapies for CRPC. Presented data are obtained from literature and congress reports updated until December 2011. Targeted therapies in advanced phases of clinical development include novel androgen signaling inhibitors, inhibitors of alternative signaling pathways, anti-angiogenic agents, inhibitors that target the bone microenvironment, and immunotherapeutic agents. Radium-223 and MDV3100 demonstrated a survival advantage in phase III trials and the road for their introduction in clinical practice is rapidly ongoing. Results are also awaited for phase III studies currently underway or planned with new drugs given as monotherapy (TAK-700, cabozantinib, tasquinimod, PROSTVAC-VF, ipilimumab) or in combination with docetaxel (custirsen, aflibercept, dasatinib, zibotentan). The optimal timing, combination, and sequencing of emerging therapies remain unknown and require further investigation. Additionally, the identification of novel markers of response and resistance to these therapies may better individualize treatment for patients with CRPC.

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